Thursday 9 April 2015

VENLAFAXINE PART 1/3

VENLAFAXINE PART 1/3

Venlafaxine structure.svg






Venlafaxine
CAS : 93413-69-5
CAS Name: 1-[2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol
Additional Names: (±)-1-[a-[(dimethylamino)methyl]-p-methoxybenzyl]cyclohexanol; N,N-dimethyl-2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethylamine; venlafexine
Molecular Formula: C17H27NO2
Molecular Weight: 277.40
Percent Composition: C 73.61%, H 9.81%, N 5.05%, O 11.54%





Venlafaxine (brand namesEffexorEffexor XR and Trevilor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class.[3][4][5] This means it increases the concentrations of the neurotransmitters serotonin and norepinephrine in the body and the brain. First introduced by Wyeth in 1993, now marketed by Pfizer, it is licensed for the treatment of major depressive disorder (MDD), generalised anxiety disorder (GAD), panic disorder and social phobia.[6][7]
Comparative efficacy and acceptability of 12 new-generation antidepressants: a multiple-treatments meta-analysis have shown venlafaxine, alongside mirtazapineescitalopram and sertraline were significantly more efficacious.[8] Remission rates (defined as a HAM-D score of 7 or less) were 58% for venlafaxine plus mirtazapine.[9]
The rate of life-threatening or lethal outcomes for suicidal overdoses of venlafaxine is lower than for the TCAsMAOIs and bupropionand comparable to several of the SSRIs.[10] It is metabolised in the body into another antidepressant drug called desvenlafaxine (O-desmethylvenlafaxine) which is also sold as an antidepressant, under the brand name Pristiq.[11]
Both venlafaxine and paroxetine have been linked to the most severe discontinuation symptomes.
In 2007, venlafaxine was the sixth most commonly prescribed antidepressant on the U.S. retail market, with 17.2 million prescriptions.[12]

Chemistry

The chemical structure of venlafaxine is designated (R/S)-1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl] cyclohexanol hydrochloride or (±)-1-[a [a- (dimethylamino)methyl] p-methoxybenzyl] cyclohexanol hydrochloride, and it has the empirical formula of C17H27NO2. It is a white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the atypical opioid analgesic tramadol, and more distantly to the newly released opioid tapentadol, but not to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs, or RIMAs.[66]


Venlafaxine
Venlafaxine structure.svg
Venlafaxine-3D-balls.png
Systematic (IUPAC) name
(RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)-ethyl]cyclohexanol
Clinical data
Trade namesEffexor XR, Effexor, Trevilor
AHFS/Drugs.commonograph
Licence dataUS Daily Med:link
  • AU: B2
  • US: C
Oral
Pharmacokinetic data
Bioavailability42±15%[1]
Protein binding27±2% (parent compound), 30±12% (active metabolite,desvenlafaxine)[2]
MetabolismHepatic (~50% of the parent compound is metabolised on first pass through the liver)[1][2]
Half-life5±2 h (parent compound for immediate release preparations), 15±6 h (parent compound for extended release preparations), 11±2 h (active metabolite)[1][2]
ExcretionRenal (87%; 5% as unchanged drug; 29% asdesvenlafaxine and 53% as other metabolites)[1][2]
Identifiers
93413-69-5 Yes
N06AX16
PubChemCID 5656
DrugBankDB00285 Yes
ChemSpider5454 Yes
UNIIGRZ5RCB1QG Yes
ChEBICHEBI:9943 Yes
ChEMBLCHEMBL637 Yes
Chemical data
FormulaC17H27NO2
277.402 g/mol





Derivative Type: Hydrochloride
CAS : 99300-78-4
Manufacturers' Codes: Wy-45030
Trademarks: Effexor (Wyeth)
Molecular Formula: C17H27NO2.HCl
Molecular Weight: 313.86
Percent Composition: C 65.06%, H 8.99%, N 4.46%, O 10.20%, Cl 11.30%
Properties: White to off-white crystalline solid from methanol/ethyl acetate, mp 215-217°. Soly (mg/ml): 572 water. Partition coefficient (octanol/water): 0.43.
Melting point: mp 215-217°
Log P: Partition coefficient (octanol/water): 0.43
Derivative Type: (+)-Form
Properties: Crystals from ethyl acetate, mp 102-104°. [a]D25 +27.6° (c = 1.07 in 95% ethanol).
Melting point: mp 102-104°
Optical Rotation: [a]D25 +27.6° (c = 1.07 in 95% ethanol)
Derivative Type: (+)-Form hydrochloride
Manufacturers' Codes: Wy-45655
Properties: Crystals from methanol/ether, mp 240-240.5°. [a]D25 -4.7° (c = 0.945 in ethanol).
Melting point: mp 240-240.5°
Optical Rotation: [a]D25 -4.7° (c = 0.945 in ethanol)
Derivative Type: (-)-Form
Properties: Crystals from ethyl acetate, mp 102-104°. [a]D25 -27.1° (c = 1.04 in 95% ethanol).
Melting point: mp 102-104°
Optical Rotation: [a]D25 -27.1° (c = 1.04 in 95% ethanol)
Derivative Type: (-)-Form hydrochloride
Manufacturers' Codes: Wy-45651
Properties: Crystals from methanol/ether, mp 240-240.5°. [a]D25 +4.6° (c = 1.0 in ethanol).
Melting point: mp 240-240.5°
Optical Rotation: [a]D25 +4.6° (c = 1.0 in ethanol)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Serotonin Noradrenaline Reuptake Inhibitor (SNRI).




1H NMR


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HSQC
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1H NMR PREDICT OF HCL



Venlafaxine hydrochloride NMR spectra analysis, Chemical CAS NO. 99300-78-4 NMR spectral analysis, Venlafaxine hydrochloride H-NMR spectrum

13C NMR PREDICT OF HCL

Venlafaxine hydrochloride NMR spectra analysis, Chemical CAS NO. 99300-78-4 NMR spectral analysis, Venlafaxine hydrochloride C-NMR spectrum







Venlafaxine

BASE



Venlafaxine NMR spectra analysis, Chemical CAS NO. 93413-69-5 NMR spectral analysis, Venlafaxine H-NMR spectrum


Venlafaxine NMR spectra analysis, Chemical CAS NO. 93413-69-5 NMR spectral analysis, Venlafaxine C-NMR spectrum





Literature References: 

Serotonin noradrenaline reuptake inhibitor (SNRI). Prepn: G. E. M. Husbands et al., EP 112669US4535186 (1984, 1985 both to Am. Home Prods.); 

and resolution of isomers: J. P. Yardley et al., J. Med. Chem. 33, 2899 (1990). Receptor binding studies: E. A. Muth et al., Biochem. Pharmacol. 35, 4493 (1986). 

HPLC determn in biological fluids: D. R. Hickset al., Ther. Drug Monit. 16, 100 (1994).

Clinical pharmacokinetics: K. J. Klamerus et al., J. Clin. Pharmacol. 32, 716 (1992). 

Clinical trial in major depression: E. Schweizer et al., J. Clin. Psychopharmacol. 11, 233 (1991). 

Review of pharmacology and clinical efficacy in depression: S. A. Montgomery, J. Clin. Psychiatry 54, 119-126 (1993). 

Clinical trial in generalized anxiety disorder: A. J. Gelenberg et al., J. Am. Med. Assoc. 283, 3082 (2000).
P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.
P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.
P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent.





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